Date published: 2025-12-8

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9-Deazaguanine (CAS 65996-58-9)

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Alternate Names:
2-Amino-1,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; NSC 344522
Application:
9-Deazaguanine is acts as a potent inhibitor of purine nucleoside phosphorylase
CAS Number:
65996-58-9
Purity:
≥95%
Molecular Weight:
150.14
Molecular Formula:
C6H6N4O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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9-deazaguanine, a nucleoside analog, exhibits potent inhibitory activity against PNP (purine nucleoside phosphorylase). As a synthetic intermediate, it plays a significant role in the production of nucleosides, nucleotides, and other biologically active compounds. Being an analogue of guanine, one of the fundamental bases in DNA and RNA, 9-deazaguanine finds utility in the synthesis of antiviral, antineoplastic, and therapeutic agents. Moreover, it offers valuable insights into the structure and function of nucleic acids, making it useful for scientific research. The synthesis method, scientific research applications, mechanism of action, biochemical and physiological effects, advantages and limitations for lab experiments, and potential future directions of 9-deazaguanine have been extensively investigated. In research applications, it has been employed to study nucleic acid structure and function, develop antiviral and antineoplastic agents, explore nucleic acid-protein interactions, and investigate the impact of mutations on nucleic acid structure and function. Although the exact mechanism of action of 9-deazaguanine remains incompletely understood, it is believed to act as a competitive inhibitor of guanine in the formation of nucleic acid structures. Additionally, it is thought to interfere with guanine binding to proteins and other molecules. The biochemical and physiological effects of 9-deazaguanine are still under investigation, but it is postulated to hinder nucleic acid structure formation and disrupt guanine-protein binding. Furthermore, it may impede DNA and RNA replication. In summary, 9-deazaguanine holds significant promise in scientific research, particularly in the realms of nucleic acid studies, drug development, and understanding the intricate relationships within nucleic acid systems. Further exploration is required to uncover its full potential and shed light on its biochemical and physiological effects.


9-Deazaguanine (CAS 65996-58-9) References

  1. Crystal structures of Giardia lamblia guanine phosphoribosyltransferase at 1.75 A(,).  |  Shi, W., et al. 2000. Biochemistry. 39: 6781-90. PMID: 10841757
  2. Substrate deformation in a hypoxanthine-guanine phosphoribosyltransferase ternary complex: the structural basis for catalysis.  |  Héroux, A., et al. 2000. Structure. 8: 1309-18. PMID: 11188695
  3. Role of the flexible loop of hypoxanthine-guanine-xanthine phosphoribosyltransferase from Tritrichomonas foetus in enzyme catalysis.  |  Munagala, N., et al. 2001. Biochemistry. 40: 4303-11. PMID: 11284686
  4. Chemical trapping and crystal structure of a catalytic tRNA guanine transglycosylase covalent intermediate.  |  Xie, W., et al. 2003. Nat Struct Biol. 10: 781-8. PMID: 12949492
  5. Fluorescence studies of calf spleen purine nucleoside phosphorylase (PNP) complexes with guanine and 9-deazaguanine.  |  Stepniak, K., et al. 2007. Nucleosides Nucleotides Nucleic Acids. 26: 841-7. PMID: 18066911
  6. Antiproliferative activity of purine nucleoside phosphorylase multisubstrate analogue inhibitors containing difluoromethylene phosphonic acid against leukaemia and lymphoma cells.  |  Glavas-Obrovac, L., et al. 2010. Chem Biol Drug Des. 75: 392-9. PMID: 20102369
  7. Solution structures of purine base analogues 9-deazaguanine and 9-deazahypoxanthine.  |  Karnawat, V. and Puranik, M. 2016. J Biomol Struct Dyn. 34: 640-52. PMID: 25894214
  8. 8-Aminoguanine Induces Diuresis, Natriuresis, and Glucosuria by Inhibiting Purine Nucleoside Phosphorylase and Reduces Potassium Excretion by Inhibiting Rac1.  |  Jackson, EK., et al. 2018. J Am Heart Assoc. 7: e010085. PMID: 30608204
  9. Small molecule-mediated allosteric activation of the base excision repair enzyme 8-oxoguanine DNA glycosylase and its impact on mitochondrial function.  |  Tian, G., et al. 2022. Sci Rep. 12: 14685. PMID: 36038587
  10. Inhibition and Mechanism of Plasmodium falciparum Hypoxanthine-Guanine-Xanthine Phosphoribosyltransferase.  |  V T Minnow, Y., et al. 2022. ACS Chem Biol. 17: 3407-3419. PMID: 36413975
  11. An Alkyne-Isocyanide Cycloaddition/Boulton-Katritzky Rearrangement/Ring Expansion Reaction: Access to 9-Deazaguanines.  |  Luo, J., et al. 2023. Org Lett. 25: 2123-2128. PMID: 36943758
  12. Purine nucleoside phosphorylase inhibitors: biochemical and pharmacological studies with 9-benzyl-9-deazaguanine and related compounds.  |  Bennett, LL., et al. 1993. J Pharmacol Exp Ther. 266: 707-14. PMID: 8355201
  13. Structure-based design of inhibitors of purine nucleoside phosphorylase. 2. 9-Alicyclic and 9-heteroalicyclic derivatives of 9-deazaguanine.  |  Secrist, JA., et al. 1993. J Med Chem. 36: 1847-54. PMID: 8515423

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

9-Deazaguanine, 25 mg

sc-217528
25 mg
$311.00